Triethylamine → HCID 14978580, compound

HRID 2256013Notes

Reaction equation

HRID 2256013 reaction equation
[C:1]([NH:4][CH:5](Br)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].CCN(CC)CC.[CH3:24][N:25]([CH3:34])[S:26]([N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1)(=[O:28])=[O:27].[Li]CCCC.[NH4+].[Cl-]>O.C1COCC1>[C:1]([NH:4][CH:5]([C:32]1[N:31]=[CH:30][N:29]([S:26](=[O:28])(=[O:27])[N:25]([CH3:34])[CH3:24])[CH:33]=1)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamide2×HCID 14860701HCID 14860701, compoundHCID 178418339Butyllithium

Product 1

HCID 14978580HCID 14978580, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a cooled (-78° C.) THF solution (150 mL) of 2-acetamido-N-benzyl-2-bromoacetamide (prepared from 2-acetamido-N-benzyl-2-ethoxyacetamide (2.00 g, 8.0 mmol) and BBr3 (1M solution in CH2Cl2, 9.0 mL, 9.0 mmol)) was added Et3N (1.62 g, 16.0 mmol), and then a THF solution of the 2-lithio salt of N,N-dimethylimidazole-1-sulfonamide (generated by the addition of n-BuLi (2.5M in hexane, 3.9 mL, 9.68 mmol) into a cooled (-78° C.) THF solution (25 mL) of N,N-dimethylimidazole-1-sulfonamide (1.54 g, 8.8 mmol)) was added during a 15 min interval. The reaction mixture was stirred at this temperature (30 min) and then at room temperature (45 min). A saturated aqueous NH4Cl solution (50 mL) and H2O (50 mL) were then sucessively added to the reaction, and the aqueous mixture was extracted with EtOAc (3×50 mL). The combined extracts were dried (Na2SO4), and the volatile materials were removed by distillation in vacuo. The residue was purified by flash column chromatography on SiO2 gel (4% MeOH/CHCl3) to give 0.50 g (17%) of the desired product: mp 145°-147° C. (recrystallized from EtOAc/hexane); Rf 0.35 (4% MeOH/CHCl3); IR (KBr) 3400, 1640, 1530, 1380, 720 cm-1 ; 1H NMR (DMSO-d6) δ 1.96 (s, C(O)CH3), 2.77 (s, N(CH3)2), 4.25 (dd, J=6.0, 15.5 Hz, CHH), 4.34 (dd, J=6.0, 15.5 Hz, CHH), 5.43 (d, J=8.0, Hz, CH), 7.19-7.30 (m, 5 PhH), 7.40 (s, C5H), 8.17 (s, C2H), 8.42 (d, J=8.0 Hz, NH), 8.67 (t, J=6.0 Hz, NH); 13C NMR (DMSO-d6) 22.42 (C(O)CH3), 37.80 (N(CH3)2), 42.11 (CH2), 51.40 (CH), 115.50 (C5), 126.64 (C4'), 126.94 (2C2' or 2C3'), 128.12 (2C2' or 2C3'), 136.70 (C2), 139.17 (C1'), 140.26 (C4), 168.93 (C(O)NH), 169.09 (C(O)CH3) ppm; mass spectrum (FD) 380 (M+ +1, 34), 248 (13), 247 (100), 108 (64).

Workup

  1. additionwas added during a 15 min interval
  2. customat room temperature
  3. custom(45 min)
  4. extractionthe aqueous mixture was extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customthe volatile materials were removed by distillation in vacuo
  7. customThe residue was purified by flash column chromatography on SiO2 gel (4% MeOH/CHCl3)

Sources & evidence

ORD record
ord-1bcde2ffb4f34466b9ff5e3d4e7d93fc
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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